4-(Iodomethyl)cyclopentene

Base Information

• Chemical Name: 4-(Iodomethyl)cyclopentene
• CAS No.: 83528-59-0
• Molecular Formula: C6H9I
• Molecular Weight: 208.042
• Hs Code.: 2903890090
• DSSTox Substance ID: DTXSID40376690
• Mol file: 83528-59-0.mol

Synonyms:4-(iodomethyl)cyclopentene;83528-59-0;4-(IODOMETHYL)-CYCLOPENTENE;Cyclopentene,4-(iodomethyl)-;4-(iodomethyl)cyclopent-1-ene;SCHEMBL1097292;DTXSID40376690;FT-0720964

Chemical Property of 4-(Iodomethyl)cyclopentene

Chemical Property:

• Vapor Pressure: 0.765mmHg at 25°C
• Refractive Index: 1.575
• Boiling Point: 190 ºC at 760 mmHg
• Flash Point: 78.9 ºC
• PSA: 0.00000
• Density: 1.706 g/cm³
• LogP: 2.38760
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 207.97490
• Heavy Atom Count: 7
• Complexity: 68.2

Purity/Quality:

99% ^*data from raw suppliers

4-(IODOMETHYL)-CYCLOPENTENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC1CI

Technology Process of 4-(Iodomethyl)cyclopentene

There total 1 articles about 4-(Iodomethyl)cyclopentene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

4-(hydroxymethyl)cyclopentene (25125-21-7) → (3-cyclopentenyl)iodomethane (83528-59-0)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 0 - 20 ℃; for 2h;

DOI:10.1002/ejoc.200300448

Reference yield:

(3-cyclopentenyl)iodomethane (83528-59-0) → exo,exo-1,3-dichlorobicyclo<2.2.1>heptane-endo-1-nitrile (115119-74-9,115183-73-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, -55 to -60 deg C; 2.) THF, HMPA, -55 to -60 deg C, 1 h, -30 deg C, 3 h

2: 87 percent / trimethyl aluminum, ammonium chloride / CH₂Cl₂ / Heating

3: 86 percent / pyridine, trifluoroacetic anhydride / tetrahydrofuran / 0 deg C, 1 h, room temp., 3h

4: 33 percent Chromat_. / CuCl, PPh₃ / benzene / 8 h / 160 - 165 °C

With pyridine; ammonium chloride; trimethylaluminum; trifluoroacetic anhydride; lithium diisopropyl amide; triphenylphosphine; copper(l) chloride; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja00224a043

Reference yield:

(3-cyclopentenyl)iodomethane (83528-59-0) → endo,exo-1,3-dichlorobicyclo<2.2.1>heptane-exo-1-nitrile (115119-74-9,115183-73-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, -55 to -60 deg C; 2.) THF, HMPA, -55 to -60 deg C, 1 h, -30 deg C, 3 h

2: 87 percent / trimethyl aluminum, ammonium chloride / CH₂Cl₂ / Heating

3: 86 percent / pyridine, trifluoroacetic anhydride / tetrahydrofuran / 0 deg C, 1 h, room temp., 3h

4: 61 percent Chromat_. / CuCl, PPh₃ / benzene / 8 h / 160 - 165 °C

With pyridine; ammonium chloride; trimethylaluminum; trifluoroacetic anhydride; lithium diisopropyl amide; triphenylphosphine; copper(l) chloride; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja00224a043

upstream raw materials:

4-(hydroxymethyl)cyclopentene

Downstream raw materials:

exo,exo-1,3-dichlorobicyclo<2.2.1>heptane-endo-1-nitrile

endo,exo-1,3-dichlorobicyclo<2.2.1>heptane-exo-1-nitrile

Refernces